Can someone please help me...and be very specific in your instructions as I am new to this whole process with e-readers / converting files!

When I try to send my book in Calibre to my kindle account, I get an error message (see below at the end of this question). The process I am using to send it is as follows:
1. Highlight book
2. Click on Connect/share icon
3. Select start content server
4. then select email to myname@free.kindle.com (I've also tried myname@kindle.com and my personal email accounts)

Then I receive this error message:

ERROR: Failed to email books: Failed to email the following books:
Switch

(10060, 'A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond')
Traceback (most recent call last):
File "site-packages\calibre\gui2\device.py", line 646, in _send_mails
File "site-packages\calibre\utils\smtp.py", line 96, in sendmail
File "smtplib.py", line 295, in connect
File "smtplib.py", line 273, in _get_socket
File "socket.py", line 514, in create_connection
error: [Errno 10060] A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond

The process I am using to send it is as follows:
1. Highlight book
2. Click on Connect/share icon
3. Select start content server
4. then select email to myname@free.kindle.com (I've also tried myname@kindle.com and my personal email accounts)

You don't need step 3. The content server has nothing to do with sending books by email.
I can't help much with step 4, but you do need to configure correctly for sending by email first. A mail server and username/password are needed.

I regularly send html files to free.kindle.com; they have to be double-zipped. Dunno how this applies to a *.prc file, which I assume is what you're sending. Indeed, a *.prc file is what I get back from Amazon from my double-zipped html file!